


Dare Me

by TammyRenH



Category: Supernatural RPF
Genre: Blow Jobs, Exhibitionism, Hand Jobs, Jared in a skirt, Kinda, M/M, bit of hair pulling, cause he'll do it, dont dare Jared, going bare
Language: English
Status: Completed
Published: 2019-09-15
Updated: 2019-09-15
Packaged: 2020-10-19 03:43:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20650646
Author URL: https://archiveofourown.org/users/TammyRenH/pseuds/TammyRenH
Summary: Written for swan_song21's excellent prompt for salt_burn_porn "I’ve seen the way you look at me when you think I don’t notice"  I don't know how I got from there to Jared in a skirt but I'm gonna blame my muse, she's twisted.Jared just can't say no to a dare, even when it leads to him wearing a cheerleader outfit and shaking his pom poms





	Dare Me

The thing about Jared is that it is hard wired into his biology that he is incapable of saying no to a dare. Tie that with his competitive nature, and it’s perfectly understandable why he is standing in front of Alpha Psi Omega’s booth during the fall festival wearing a cheerleader’s outfit.

The skirt is short, like really short, barely covering Jared’s boxer’s short, and if he wasn’t in Texas, he’d be freezing his ass off.

But the gimmick worked, the Alpha Psi Omega’s booth, which is selling candied and caramel apples, is outselling the other booths ran by the other societies. 

“Jesus, we are going to have to put you in a skirt more often.” Chad said as he made yet another sale. Jared’s job was to attract people to the booth, he had just come back from walking around the festival, shaking pom poms and loudly exhorting the value of the apples. Quite a crowd followed him back, which made all the catcalls and wolf whistles worth it . “Do you think you could wear that get up when I meet with my Ethics professor next week?”

“I think your Ethics professor would immediately fail you if I did.” Jared tugged at the skirt, trying in vain to inch it a bit lower. “This looked longer on Amazon.”

“Because it was made for someone human sized, not someone with legs the size of a tall maple.” Chad commented. Chad winked at the girl waiting for her candied apple who was giggling with her group of friends. “Doesn’t he look good girls? Speaking of trees, you can thank me for him shaving that forest that was growing on his legs. Smooth as a baby’s bottom now. Go ahead and feel – he won’t mind.”

The girls kept giggling, side eying Jared as they did so. Jared flipped Chad the bird. Chad had indeed talked Jared into shaving his legs, although to be fair it wasn’t hard to talk Jared into anything after he had a few beers. There were a few nicks along the way, but once he got over the weird alien feeling of it all, he like how his shaved legs felt – especially how they felt in the cheerleader’s skirt.

“Well, if they won’t feel, I will.” A deep, Southern-sweetened voice came from behind him. Jared was already flushing before he turned around, he’d recognize that voice anywhere. Jensen Ackles was standing beside him, dressed like a cowboy, Western hat, chaps over his jeans, his well-worn brown cowboy boots on his feet. He looked like every wet dream Jared had ever had.

Jared was normally a loud and boisterous type of guy, especially among his friends and fellow members of the Alpha Psi Omega society. But around Jensen – a senior, so self-assured, so beautiful it should be illegal – Jared was shy and tongue-tied.

As Jensen’s finger trailed the bare skin right above his knee, Jared shivered. Jensen looked at him, eyebrows raised. Jared could feel himself blushing. Three hours of parading around the festival, shaking pom poms, and proudly twirling around in his skirt and not a single blush, not a hint of one. Two seconds in the company of Jensen and Jared was blushing like a 12-year-old meeting her dreamboat crush.

“Hey Jensen, we fucking did it man. We got the most money out of anyone here. They will now have to bow down to our superiority.” Chad, who was not the least bit shy around Jensen, or anyone in the known universe, proudly held up the money box.

“You know that money is going to charity, right? Toys for Tots. It’s not actually our money.” Jensen told him, taking his eyes off Jared which gave Jared the chance to take a few deep, hopefully calming breaths. 

Chad shrugged. “Don’t matter. We still fucking won.”

“Well I think that is cause for a celebration then.” Jensen said brightly. “What do you say Jared, you want to go with me to the county line and pick up a keg for the party tonight?”

Richardson County was a dry county, which made absolutely no sense since it was also a college town, but it was the South – what could you do? The nearest wet county was thirty minutes to the north. Some enterprising person had built a liquor store right at the county line almost half a century ago. It was still the go to place for young college students wanting to buy booze.

“I can’t actually buy beer, not old enough.” Jared admitted, looking down at his tennis shoes to avoid staring at Jensen. Sometime during the day, they had come untied, laces trailing in the grass. It was a miracle he hadn’t tripped on them, as graceful as he was.

“But I can.” Jensen patted him on the shoulder, then gave his upper arm a squeeze. “Nice. I hereby designate you my muscle man. I’m buying, you are doing the heavy lifting.”

Jared had never been alone with Jensen before, it was a dizzying prospect. 

From the first time he met him, in September just as he had begun his freshman year of college, at the tryouts for Phantom of the Opera, Jared had crushed on Jensen. But Jensen was probably straight, and even if not, was far out of his league.

Jensen had won the role of the Phantom, like of course he had. And Jensen played the dark, possessive, menacing character very, very, very well. It was a shame that someone as pretty as Jensen had his face covered by a mask but damn – every night for six weeks Jared had fallen asleep dreaming he was Christine. Jared had been the assistant stage manager for the production, he hadn’t had the nerve to tryout after seeing Jensen’s audition. It was blissful torture to stand there, side by side with Jensen while Jensen waited to go onstage. At the cast parties, Jared had found himself talking to everyone, dancing with whoever would go on the dance floor with him, as Jensen held court in a corner of the room At some point every person at the party would pay homage to Jensen, bring him drinks, sit down and talk with him a bit, smoke a joint with him. And Jared had always tried to work up the nerve to approach him but had to settle for staring wistfully at him from afar.

And now suddenly, he was being offered a chance to be alone with Jensen. Thirty miles there, thirty miles back. Fuck, what in hell would he find to talk about?

“Let me change real quick – “ Jared started. He handed the pom poms to Felicia who was in the booth with Chad. She gave him a look like what the hell am I supposed to do with these. Jared ignored her.

“No, sorry Jared, there’s not enough time for that.” Jensen replied, not looking the least bit sorry. “I’m leaving now so if you are going – “

“Yeah, yeah.” Jared smoothed the skirt down in a vain attempt to cover his knees. What the hell, it was Halloween. Let people stare, he wasn’t about to give up a chance to be alone with Jensen. He followed Jensen out to his car.

Jensen’s car was black, sleek, classic.

Jensen had the radio turned to the oldies station, classic rock low and rumbling. Jared wanted to say something about his choice in music but decided against it. He would probably end up saying something stupid. Instead he bit his lip and looked out the window as Jensen made his way off campus and headed north out of town.

Jared thought of and discarded three different topics of conversation before he was startled out of his thoughts by the feel of fingers rubbing just below his knee. “Smooth.” Jensen commented. 

Jared shifted in his seat, a nervous kind of flutter in his stomach. “What are you doing?” He asked, his voice definitely not an octave higher than it usually was.

“Seeing if you are smooth all over.” Jensen’s fingers played with the hem of Jared’s skirt, slipping a fingertip inside of it. Jared nervously looked to his side, afraid someone could see, but traffic was passing them by, unaware.

“Are you?”

Jensen’s fingers were rubbing on his upper thigh. Jared’s brain was short circuiting, torn between wanting to push Jensen’s hand away and slide down in the seat so Jensen’s fingers could reach further up his skirt. His face was red, his breathing sounded loud to him. “Am I what?”

Jensen chuckled. His eyes flickered to Jared before focusing on the road again. “Smooth all over. What else were we talking about?”

Had they been talking about that? What the hell could he possibly mean by – Jensen traced his fingertips over the material covering one of Jared’s balls – oh. Fuck.

“No, of course – Jesus.” Jared said, squirming a bit more. “Shouldn’t you have both hands on the wheel?”

“Traffic is light now that we are out of town. Sides I’ve seen the way you’ve look at me. Do you really want me to stop?” His hand pressed against Jared’s cock, which had become very interested in all the touching.

“How do I look at you?” Jared asked. Jensen’s fingers were leaving little lines of heat wherever they touched. No, he didn’t want him to stop.

“Like you are starved.” Jensen answered and then. “Take off your panties, why don’t you?”

“I don’t have – I don’t own – I’m not - “ Jared felt like an inferno was inside of him, he felt hot and uncomfortable and twisty inside. “I am wearing boxers.”

Fingers inside his skirt again, lightly tugging on the hem of his boxers. “Pity. I would still like you to take them off though.”

“No.” A car passed by headed on the other direction. “Why?” 

“Because I’d like to see if you are smooth all over.” Jensen said, pronouncing every word succinctly, like Jared was a very slow learner. 

“I already told you I’m not.” Jensen’s fingers were tracing inside his boxers, Jared could swear he could feel his dick straining to reach them.

“I’d like to feel for myself.” Jensen looked back over and gave him a wink. “If that’s okay with you that is.”

Yeah, that was not happening. Not in the car. Not in the open like this. And he was just going to ignore how much his cock liked the idea. 

“I dare you to take your boxers off right now.” Jensen added.

Fuck.

“You’ve been talking to Chad.” Jared grumbled.

“So are you going to back down from a dare or are – “

Before Jared could second guess himself or talk himself out of it, he lifted his hips up and very quickly pulled the boxers down until they reached his thigh. The boxers were cherry red. He was pretty sure his face was redder. At least his skirt still covered everything.

“Good boy.” Jensen said approvingly, fingers teasing the tip of his very happy to be freed and eager to show it cock. “But the dare was to take them all the way off. “

There was no reason to do what Jensen asked. He wasn’t scared of Jensen; they weren’t dating, and Jared wasn’t into exhibitionism. And yet Jared kicked his still untied sneakers off and after checking to make sure no vehicle was beside him, pulled the boxers the rest of the way off.

“Happy now?” Jared asked, trying not to show just how aroused all this had made him.

“Almost as happy as you are.” Jensen was smirking and as they stopped for a red light, he reached inside the skirt and wrapped his hand around Jared’s cock. 

If it weren’t for the seat belt, Jared would have lifted himself straight up to the top of the car. He couldn’t look around; he just knew that someone in a big truck was looking down and grinning but even that thought didn’t stop pre-come from dripping out of the tip of his cock. Fuck. 

The rest of the trip went by in a blur. Jensen’s fingers touched and teased, they retreated and came back. They rubbed circles on his upper thigh, they skittered over his balls, they rubbed the tip of Jared’s penis and Jared was pretty sure he was going to explode.

When he saw the town of Preston coming up, he reached down to pick up the boxers. He was equal parts relieved about putting them back on and just as sad about it. He really liked the way Jensen’s hands felt on him, even with the fear that someone would see what they were doing. Maybe because someone might see what they were doing. Jared’s head was in quite the spin, it was hard to tell which way was up.

“Leave them off.” Jensen said. “You are wearing a skirt, no one is going to know if something is underneath it or not.”

“Another dare?” Jared asked, still bent over, hands on boxers, unsure.

“No, do it because I want you to.” Jensen said, he was pulling into S&D’s Liquor store. “Do it because I think it would be fucking hot.” Jensen’s voice was deep, almost growly. Jared shoved the boxers underneath the seat and pulled on his sneakers, tying them quickly so he didn’t fall and land ass up because that would just be his luck. Jensen smiled at him and it was so intoxicating that Jared wondered if there was anything he wouldn’t do to be gifted with that smile. It was too early in this – relationship? – for Jared to be this head over heels but whatever. Jared carefully got out of the car and followed Jensen into the store.

Jared swore he could feel air coming from the store’s wood floor right up to his groin. He had a sudden vision of Marilyn Monroe, skirt flying up and it was all he could do not to put his hands on the hem and hold the skirt in place He followed Jensen so closely that he was almost tripping over the heel of Jensen’s boots. 

“I’ve got this.” Jensen indicated the beer. “Why don’t you go over there and pick us up some Jack Daniels?”

Jared wasn’t the only one in costume, it was Halloween after all, but definitely the only male in a skirt. It had gotten him a few looks, some admiring, some not so much.

Jared hated leaving the sanctuary of Jensen’s side, he could tell by the self-satisfied smile Jensen was giving him that Jensen knew that. But he squared his shoulders and made his way to where the whiskey was. And if he slightly swayed his hips on the way, well Jared might not be as experienced as Jensen, but he did know when someone was checking out his ass.

He had just grabbed the bottle when he felt a pressure on his back, lips close to his ear. There was a tuft of air blown, sending a shiver down Jared’s body. “You look so pretty in that skirt Jared. I can’t decide if it’s your ass that I like looking at, or the way that your skirt is tenting in front because of how hard your dick is.”

Fuck.

Jared passed the Jack Daniels to Jensen, scared he was going to drop it. Jensen laughed and pulled away. He had the keg in a cart and added another bottle of Jack to the one Jared had given him. 

Jared rushed out of the liquor store, too mortified to look anyone in the eye. He was waiting by the car, fighting the urge to cover his election with his hand, when Jensen made it out with the liquor.

They were on their way back, and Jared was still blushing, squirming in his seat. He really should put his boxers back on.

“So,” Jensen said, voice casual as if he hadn’t been the cause of the most mortifying moment of Jared’s life. “I need to make a detour and I bet that I can get you off before we reach it.”

Jared shifted in the seat. Jensen had put a towel on it before Jared sat down, probably because he didn’t want Jared’s bare ass rubbing all over his seat. The towel was bit scratchy, and it was intensifying the heat Jared was feeling. “How far to the detour?” 

“You’ll find out.” Jensen’s fingers reached under the skirt again and traced Jared’s cock, from the tip down to the balls. Jared’s shirt rode up, just an inch shy of showing everything Jared had.

“Such a nice cock.” Jensen commented. “Can’t wait to get my mouth on that big boy.”

Just the thought of Jensen’s mouth on his cock had Jared on edge, cock now fully hard. He was shifting, unable to get comfortable, the towel rubbing against his ass, Jensen’s fingers too light on his cock.

Jared reached for his cock with his own hand, the need was building and there was no way he was walking on to campus with a hard on this obvious, but Jensen batted his hand away. “I’ll take care of you,” he promised.

The tip of his cock was leaking pre-come in embarrassingly copious amounts. Jensen’s finger traced over the tip, a fingernail scraped over Jared’s slit and Jared gasped. Jensen’s whole hand was on his cock now, sliding all the way up. The glide was rough, but Jared’s cock didn’t care. Jared could already feel his balls began to draw up, he had been on edge for what seemed like forever.

“Come on Jared.” Jensen said. His eyes were still on the road, one hand steady on the wheel. The other was beginning to pump Jared’s cock faster, even with the pre-come Jensen had gathered on his fingers it was a rough slightly painful glide but holy hell –

Jensen turned his head toward Jared, licking those plush lips of his and then grinned as he turned back to the road and twisted the head of Jared’s cock and that was it –

Jared was coming all over Jensen’s hand, the towel, the skirt. His whole body was shaking from the strength of the orgasm.

“Fuck.” 

“Yeah, that truck driver really enjoyed it too I think.” Jensen said as he turned the car down a dirt road.

Jared turned his head quickly, but the highway was already hidden by trees. “You fucker.” There was no heat in the words. Jared was too blissed out for heat. “Where are we going?”

“Middle of nowhere.” Jensen said, taking a path that shook the car it was so rough, stopping behind a line of trees. There was a burnt-out field behind them, and nothing but trees in front. “I have a problem I need your help with.”

Jared looked over and Jensen’s erection was just as obvious in his tight jeans as Jared’s had been. The chaps seemed to frame Jensen’s groin area, making the way his cock pushed against the fabric even more obvious. Hell yeah, Jared could help with that.

Jared got out of the car, wiping as much the come as he could off his thighs with the towel and throwing it in the backseat. The skirt was a lost cause, he was going to have to find a way to sneak into his dorm room to change before the party but that was a problem for later.

Jensen came over to his side, palming his still jean-covered erection. “You don’t have to if you don’t want to. This isn’t a quid pro quo kind of situation.” 

Jared responded by sinking down to his knees. “I want to.” 

Jensen unbuckled his belt and very carefully unzipped his jeans before pulling them and his boxers down just enough for his cock to be freed. 

“I’ve seen the way you look at me.” Jensen repeated the words from earlier, voice sultry and deep. “Like a man starved. Is that what you were hungry for?”

In answer, Jared flitted out his tongue, licking the tip of Jensen’s cock. There was pre-come there, it tasted a bit salty, a bit bitter, but not bad. He ran his hand down the length of Jensen’s cock. It was a nice cock, thick, hard. Jensen’s own hands were by his side, but they were twitching. Jared knew what he wanted.

He lifted his head, met Jensen’s eyes. “Go ahead, I like getting my hair pulled.”

“Fuck. You’re perfect Jared.” One of Jensen’s hands immediately grabbed onto his hair, gripping and releasing. Jared took a moment to enjoy the little slivers of pain and then went back to work in earnest. He swallowed Jensen’s cock all the way down, until it hit the back of his throat. Jared could feel his eyes watering as he held Jensen’s cock there, swallowing against his gag reflex, feeling Jensen’s cock pulse inside his mouth. Jensen was alternating between running his fingers through Jared’s hair and tugging lightly, urging him to go further.

“So good Jared,” Jensen’s voice was ragged, he was breathing hard and Jared felt a swell of pride that he was affecting him this way.

Jared bobbed up, taking a deep breath. He mouthed at the tip again, licking at the wetness, finding he liked the taste better this time. He sucked at just the tip and Jensen groaned above him.

“Come on baby, take me all the way.” Jensen urged.

Another deep breath and Jared did take Jensen all the way down, gag reflex not as bad this time. He sucked and his tongue licked whatever part of Jensen’s cock it could reach, his world melted down to Jensen and the smell and the taste of him. Jensen’s balls were tickling his nose, Jensen was cursing up above him.

Jared pulled off again, taking a moment to breathe.

“Once more time baby okay?” Jensen asked. “I’m so close.”

And Jared did, this time when his mouth was full, he began to hum, knowing from experience what the vibrations would do to Jensen. Jensen’s hand fisted in Jared’s hair, there was a tug and Jared groaned around Jensen’s cock. Jensen cursed again and then came without warning, come filling Jared’s mouth, so much of it that Jared couldn’t swallow it all. Jared pulled back, wiping it from his chin.

Jensen pulled him up into a kiss, apparently not caring he was tasting his own come. It was weird to think this was their first kiss, after the hand job and the blow job but then Jared couldn’t think at all, letting himself drown in the pleasure of Jensen’s lips on his, his tongue inside his mouth, his teeth biting into Jared’s lower lip.

“That was amazing Jared. Thank you.” Jensen wiped a bit of come off Jared’s cheek . “It’s getting late, I guess we’d better get back.”

“Yeah, sure.” Jared moved away, not meeting Jensen’s eyes. Apparently, all Jensen wanted from him was to get off, Jared probably should be grateful Jensen got him off first . 

“Hey, this isn’t a wham, bam thank you sir kind of thing.” It was as if he was reading his mind. Jensen’s hand was rubbing his arm. “Saturday night I’d like to take you to a nice place for dinner and to a movie and maybe we could go back to my place, share the Jack.”

“You want to date me?” Jared asked, a bit shocked. He really thought this was a one off.

“Yeah Jared, I want to date you. I’d like to get to know you better.”

They were headed to the car. Jared pulled his boxers out of under the seat and shimmied them on. Jensen looked regretful but didn’t say anything.

Jared wondered if Jensen’s sudden interest in him was because of the skirt. He hoped Jensen wasn’t expecting him to wear one Saturday. “I don’t usually wear women’s clothes you know. Will you still be into me when I am wearing jeans?” He asked, trying for a light tone as they got into the car.

“Will I want to get into your pants as much as I wanted to get under your skirt?” Jensen asked, tires pealing as he headed back to the dirt road. “Hell yeah.”

A hand reached out again, but this time it was to grab Jared’s.

“Just so you know, while you were looking at me and thinking I wasn’t noticing, I was looking right back.” Jensen said and squeezed Jared’s hand.

Jared looked out the window into the gathering darkness. He had dried come on his thighs, probably on his face, and his skirt was ruined. Oh, and the gorgeous man beside him was now his boyfriend.

“Hey Jared,” Jared turned his head back toward said gorgeous man. “I dare you to wear panties Saturday night.”

And his cheeks were flushing again. “I thought we established I’m not a cross dresser.”

“Oh, we did.” Jensen glanced over, heat in his eyes. “I just like watching you squirm.”

Fuck.


End file.
